Solo or small team? Then you know the drill: 40 chat threads, half-finished docs, and no clear next step. In this episode, Samim Safaei, co-founder of SIIFT.AI, breaks down how their “Founder’s Compass” turns messy ideas into structured, repeatable validation — without losing speed.

We cover:

• Why generic chat tools say “yes” to everything — and how SIIFT removes the fluff
• The real blocker: information architecture (not another app)
• Guided chat plus a structured canvas: brain dump in, clean strategy out
• What beta users taught the team about UX, education, and overwhelm
• Partnerships with accelerators and mentors to scale guidance (not replace it)
• Privacy and IP: why paying for software beats paying with your data
• Go-to-market goals, pricing philosophy, and where SIIFT goes next

Guest: Samim Safaei — Co-founder, SIIFT.AI Topics: Early-stage ops, validation, founder workflows, AI tooling, product UX

Learn more: siift.ai Connect with Samim: LinkedIn (search “Samim Safaei”)

If this episode saved you from another “where did I write that?” moment, share it with a founder friend and subscribe for more no-BS playbooks for building from zero to one.

Most people underestimate nonprofits. They’re not small or slow—they’re a $400B U.S. engine (trillions globally) that run on trust. Our guest Cyrus Kazi, co-founder & CEO of Quantably, explains why trust is a data problem—and how his team built an “operating system for impact” that finally connects collection, analysis, and reporting.

We cover:

• The multi-tool mess: why orgs juggle 17–25 disconnected apps—and what to do first
• Data strategy > data entry: collecting only what serves outcomes (Theory of Change, operationalized)
• Quantably’s “Impact LLM”: automated analysis for CEOs, CFOs, fundraisers—no stats degree required
• Reporting that donors believe: SROI, audit-ready narratives, and younger data-native donors
• GTM that works in this sector: partner channels (auditors, fundraising consultants) over cold outreach
• The future: why “data entry” dies this decade—replaced by conversational capture and inference
• Founder lessons: go to market right vs fast, vision-aligned teams, and knowing your limits

Guest: Cyrus Kazi — Co-founder & CEO, Quantably Topics: Nonprofit ops, impact measurement, data strategy, SROI, AI for social good

Learn more: quantably.com

Connect with Cyrus: LinkedIn (search “Cyrus Kazi”) | Email: ckazi@quantably.com

Sick of living in your calendar? Founder Dario De Santis (Tweenlin) breaks down how his team is cutting the meeting overload—turning endless 1:1s and “quick syncs” into fast, human conversations without scheduling gymnastics.

We dig into:

• The real cost of meeting sprawl (and why remote work made it worse)
• How Tweenlin’s AI deflects 1:1s and small-group meetings into on-the-fly conversations
• What early pilots show: measurable productivity gains and “empty calendar” serenity
• Selling true workflow change into 10k–100k-person enterprises
• Why you don’t fail if you don’t give up: Dario’s 4-year founder journey from idea → Gartner “Cool Vendor”

If your team complains about meetings, send them this.

Guest: Dario De Santis — Founder & CEO, Tweenlin Topics: AI collaboration, meeting reduction, enterprise workflow, remote culture, productivity

Connect with Dario: LinkedIn (search “Dario De Santis”) Learn more: Tweenlin

Subscribe for more founder playbooks on building the future of work.